Cesium fluoride → HCID 66984753, compound

HRID 1009656Notes

Reaction equation

HRID 1009656 reaction equation
[CH:1]1([CH:4]([O:6][C:7](=[O:39])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:16]([CH:35]4[CH2:38][CH2:37][CH2:36]4)[C:17]4[C:22]([C:23]=3[C:24]#[N:25])=[CH:21][CH:20]=[C:19](B3OC(C)(C)C(C)(C)O3)[CH:18]=4)=[CH:11][CH:10]=2)[CH3:5])[CH2:3][CH2:2]1.Cl[C:41]1[N:46]=[CH:45][CH:44]=[CH:43][N:42]=1.[F-].[Cs+]>COCCOC.CCOC(C)=O.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>[CH:1]1([CH:4]([O:6][C:7](=[O:39])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:16]([CH:35]4[CH2:38][CH2:37][CH2:36]4)[C:17]4[C:22]([C:23]=3[C:24]#[N:25])=[CH:21][CH:20]=[C:19]([C:41]3[N:46]=[CH:45][CH:44]=[CH:43][N:42]=3)[CH:18]=4)=[CH:11][CH:10]=2)[CH3:5])[CH2:2][CH2:3]1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 744042-ChloropyrimidineHCID 66985065HCID 66985065, compound

Product 1

HCID 66984753HCID 66984753, compoundYield 92.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of {4-[3-cyano-1-cyclobutyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indol-2-yl]-phenyl}-carbamic acid 1-cyclopropyl-ethyl ester (0.2 g, 0.38 mmol), 2-chloropyrimidine (39 mg, 0.34 mg), Pd(PPh3)4 (22 mg, 0.095 mmol) and cesium fluoride (0.116 g, 0.76 mmol) in DME (2.0 mL) was stirred at 100° C. for 16 h. The mixture was then diluted with EtOAc (20 mL), washed with water and brine, dried over Na2SO4, concentrated and purified on silica gel (CH2Cl2/EtOAc) to provide [4-(3-cyano-1-cyclobutyl-6-pyrimidin-2-yl-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester as a solid (0.15 g, 82%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. custompurified on silica gel (CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-10d481ef0b6a47ddbcba3e774a7b877b
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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