Triethylamine → HCID 67155901, compound

HRID 2196655Notes

Reaction equation

HRID 2196655 reaction equation
[F:1][C:2]1[C:29]([NH:30][S:31]([CH2:34][CH2:35][CH3:36])(=[O:33])=[O:32])=[CH:28][CH:27]=[C:26]([F:37])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:15](I)=[CH:14][N:13]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:10]2=[N:11][CH:12]=1)=[O:5].[CH:38]([B-](F)(F)F)=[CH2:39].[K+].C(N(CC)CC)C>CC(O)C.C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:1][C:2]1[C:29]([NH:30][S:31]([CH2:34][CH2:35][CH3:36])(=[O:33])=[O:32])=[CH:28][CH:27]=[C:26]([F:37])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:15]([CH:38]=[CH2:39])=[CH:14][N:13]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:10]2=[N:11][CH:12]=1)=[O:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 67155879HCID 67155879, compound

Product 1

HCID 67155901HCID 67155901, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 22597222Tetrahydrofuran 2-propanolSolvent

Conditions

Temperature
70 °C

Procedure

2,6-Difluoro-N-(3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.050 g, 0.076 mmol), potassium vinyltrifluoroborate (0.012 g, 0.091 mmol), triethylamine (d. 0.726; 0.011 mL, 0.076 mmol) and PdCl2(dppf)*DCM (0.0031 g, 0.0038 mmol) were dissolved in 3:1 IPA/THF (1.0 mL), degassed with argon for 10 minutes and heated to 70° C. overnight. The solution was partitioned between water and EtOAc. The organic portion was washed with water (3×), brine, dried over Na2SO4 and concentrated. The resulting residue was purified by column chromatography (2:1 hexane/EtOAc) giving 2,6-difluoro-N-(1-(phenylsulfonyl)-3-vinyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (57%).

Workup

  1. customdegassed with argon for 10 minutes
  2. customThe solution was partitioned between water and EtOAc
  3. washThe organic portion was washed with water (3×), brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by column chromatography (2:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-ce70202b99da4304b67276d0b1d058bb
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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