Chloroacetaldehyde → HCID 59129491, compound

HRID 1908567Notes

Reaction equation

HRID 1908567 reaction equation
[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:14][C:15]([C:17]3([C:20]4[CH:30]=[CH:29][C:23]5[O:24][C:25]([F:28])([F:27])[O:26][C:22]=5[CH:21]=4)[CH2:19][CH2:18]3)=[O:16])[CH:11]=2)[N:6]1[CH2:31][CH2:32]C#N)([CH3:4])([CH3:3])[CH3:2].[Cl:35]CC=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:14][C:15]([C:17]3([C:20]4[CH:30]=[CH:29][C:23]5[O:24][C:25]([F:28])([F:27])[O:26][C:22]=5[CH:21]=4)[CH2:19][CH2:18]3)=[O:16])[CH:11]=2)[N:6]1[CH2:31][CH2:32][Cl:35])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59129217HCID 59129217, compound

Product 1

HCID 59129491HCID 59129491, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-tert-butyl-1-(2-cyanoethyl)indolin-5-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (71 mg, 0.17 mmol) in anhydrous dichloromethane (1 mL) was added chloroacetaldehyde (53 μL, 0.41 mmol) at room temperature under N2. After 20 min of stirring, NaBH(OAc)3 (90 mg, 0.42 mmol) was added in two portions. The reaction mixture was stirred overnight at room temperature. The product was purified by column chromatography on silica gel (2-15% ethyl acetate/hexanes) providing N-(2-tert-butyl-1-(2-chloroethyl)indolin-5-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (51 mg, 63%).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. customThe product was purified by column chromatography on silica gel (2-15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-dc4dd6115bcd4220ab2487632374a5c6
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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