Allyl Alcohol → HCID 57989993, compound

HRID 239505Notes

Reaction equation

HRID 239505 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].B1C2CCCC1CCC2.Cl[C:15]1[N:20]=[C:19]([C:21]2[S:25][C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])=[N:23][C:22]=2[C:30]2[C:31]([F:48])=[C:32]([NH:36][S:37]([C:40]3[C:45]([F:46])=[CH:44][CH:43]=[CH:42][C:41]=3[F:47])(=[O:39])=[O:38])[CH:33]=[CH:34][CH:35]=2)[CH:18]=[CH:17][N:16]=1.C([O-])([O-])=O.[K+].[K+]>O1CCCC1.CN(C)C=O.CCOC(C)=O.[NH4+].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:29][C:26]([C:24]1[S:25][C:21]([C:19]2[CH:18]=[CH:17][N:16]=[C:15]([CH2:3][CH2:2][CH2:1][OH:4])[N:20]=2)=[C:22]([C:30]2[C:31]([F:48])=[C:32]([NH:36][S:37]([C:40]3[C:41]([F:47])=[CH:42][CH:43]=[CH:44][C:45]=3[F:46])(=[O:38])=[O:39])[CH:33]=[CH:34][CH:35]=2)[N:23]=1)([CH3:27])[CH3:28]

Participants

10

Reactant 4

HCID 7858Allyl AlcoholHCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 57989782N-(3-(5-(2-chloro-4-pyrimidinyl)-2-(1,1-diethylethyl)-1,3-thiazol-4-yl)-2-fluoraphenyl)-2,6-difluorobenzenesulfonamide

Product 1

HCID 57989993HCID 57989993, compound

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of 2-propen-1-ol (0.038 ml, 0.557 mmol) in tetrahydrofuran (1 ml) at 0° C. was added 9-BBN (3.34 ml, 1.670 mmol). The reaction mixture taken out of the ice bath and stirred for 2 h and added a solution of N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (0.15 g, 0.278 mmol), K2CO3 (0.742 ml, 2.226 mmol), and bis(tri-t-butylphosphine)palladium (0) (0.014 g, 0.028 mmol) in N,N-dimethylformamide (1 ml) and stirred for 30 minutes. The reaction mixture was heated to 50° C. After 4 h, the reaction was diluted with EtOAc and saturated NH4Cl. The mixture was extracted 2× with EtOAc, dried over MgSO4, filtered, and concentrated. The crude mixture was placed on silica gel and chromatography (0 to 80% DCM/MeOH, gradient) to obtain the title compound (157 mg, 42%. 1H NMR (400 MHz, DMSO-d6) ppm 10.88 (s, 1H), 8.47 (d, J=5.49 Hz, 1H), 7.67 (m, 1H), 7.43 (m, 2H), 7.31 (t, J=7.78 Hz, 1H), 7.23 (t, J=9.06 Hz, 2H), 6.62 (d, J=5.31 Hz, 1H), 4.51 (m, 1H), 3.46 (m, 2H), 2.86 (m, 2H), 1.87 (m, 2H), 1.41 (m, 9H); MS (ESI): 563 [M+H]+.

Workup

  1. stirringstirred for 30 minutes
  2. waitAfter 4 h
  3. extractionThe mixture was extracted 2× with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cb93372b713a482d9f4e1730598f7577
Source dataset
uspto-grants-2014_02
Patent number
US08642759B2

Reaction notes

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