Water → HCID 16654990, compound

HRID 1009659Notes

Reaction equation

HRID 1009659 reaction equation
[CH:1]1([C@H:4]([O:6][C:7](=[O:31])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:16]([CH:27]4[CH2:30][CH2:29][CH2:28]4)[C:17]4[C:22]([C:23]=3[C:24]#[N:25])=[CH:21][CH:20]=[C:19]([OH:26])[CH:18]=4)=[CH:11][CH:10]=2)[CH3:5])[CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:39]1[N:44]=[CH:43][CH:42]=[CH:41][N:40]=1.O>CN(C=O)C>[CH:1]1([C@H:4]([O:6][C:7](=[O:31])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:16]([CH:27]4[CH2:28][CH2:29][CH2:30]4)[C:17]4[C:22]([C:23]=3[C:24]#[N:25])=[CH:21][CH:20]=[C:19]([O:26][C:39]3[N:44]=[CH:43][CH:42]=[CH:41][N:40]=3)[CH:18]=4)=[CH:11][CH:10]=2)[CH3:5])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 744042-ChloropyrimidineHCID 59430598HCID 59430598, compound

Product 1

HCID 16654990HCID 16654990, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (R)-[4-(3-cyano-1-cyclobutyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester (0.083 g, 0.2 mmol), Cs2CO3 (0.163 g, 0.5 mmol), 2-chloropyrimidine (0.046 g, 0.4 mmol) in DMF (2.0 mL) was stirred at 70° C. for 2 h. After cooling to room temperature, the mixture was poured into water (15 mL) and the precipitate was collected via filtration and washed with water, purified on silica gel (CH2Cl2/EtOAc, 9.5:0.5) to provide (R)-{4-[3-cyano-1-cyclobutyl-6-(pyrimidin-2-yloxy)-1H-indol-2-yl]-phenyl}carbamic acid 1-cyclopropyl-ethyl ester (0.073 g, 74%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was collected via filtration
  3. washwashed with water
  4. custompurified on silica gel (CH2Cl2/EtOAc, 9.5:0.5)

Sources & evidence

ORD record
ord-a7aaac6d1916491fb03d8f2af392f39e
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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