N-bromobutanimide → HCID 86610212, compound

HRID 1685585Notes

Reaction equation

HRID 1685585 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([F:18])=[CH:15][CH:16]=2)[N:11]([CH2:19][CH:20]2[CH2:22][CH2:21]2)[CH:10]=1)=[O:8].[Br:23]N1C(=O)CCC1=O>CC(O)=O>[Br:23][C:5]1[S:1][C:2]([NH:6][C:7]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([F:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH:20]3[CH2:22][CH2:21]3)[CH:10]=2)=[O:8])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59513956HCID 59513956, compound

Product 1

HCID 86610212HCID 86610212, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Cyclopropylmethyl-6-fluoro-1H-indole-3-carboxylic acid thiazol-2-ylamide (2.5 mmol), N-bromosuccinimide (6 mmol) was stirred in HOAc (25 mL) over night at room temperature. The reaction mixture was evaporated to dryness and the crude product was purified by flash chromatography (Horizon, EtOAc-heptane) to give 1-cyclopropylmethyl-6-fluoro-1H-indole-3-carboxylic acid (5-bromo-thiazol-2-yl)-amide in 32% yield. A solution of 1-cyclopropylmethyl-6-fluoro-1H-indole-3-carboxylic acid (5-bromo-thiazol-2-yl)-amide (0.2 mmol), p-cresol (0.2 mmol) and potassium-t-butoxide (0.44 mmol) in DME (3 mL) was heated in a closed vessel in a Smith Creator microwave oven for 300 s at 120° C. Addition of water followed by extraction with DCM, drying of the organic phase followed by purification by preparative HPLC (Method E) gave the title compound.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe crude product was purified by flash chromatography (Horizon, EtOAc-heptane)

Sources & evidence

ORD record
ord-41abb3ab8294434cafb537be791b0c02
Source dataset
uspto-grants-2012_04
Patent number
US08148413B2

Reaction notes

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