Boron tribromide → HCID 69229696, compound

HRID 40093Notes

Reaction equation

HRID 40093 reaction equation
C([O:8][CH2:9][C@H:10]1[CH2:14][O:13][C:12]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]([C:34]([NH:36][CH2:37][C:38]4[CH:43]=[CH:42][C:41]([F:44])=[C:40]([F:45])[CH:39]=4)=[O:35])=[C:20]([CH:31]([CH3:33])[CH3:32])[N:21]3[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[CH:17][CH:16]=2)=[N:11]1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[F:45][C:40]1[CH:39]=[C:38]([CH:43]=[CH:42][C:41]=1[F:44])[CH2:37][NH:36][C:34]([C:19]1[C:18]2[C:22](=[CH:23][C:15]([C:12]3[O:13][CH2:14][C@H:10]([CH2:9][OH:8])[N:11]=3)=[CH:16][CH:17]=2)[N:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[C:20]=1[CH:31]([CH3:33])[CH3:32])=[O:35]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69229142HCID 69229142, compound

Product 1

HCID 69229696HCID 69229696, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following General Procedure H, (S)-6-(4-(benzyloxymethyl)-4,5-dihydrooxazol-2-yl)-N-(3,4-difluorobenzyl)-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide was prepared (10 mg, 0.015 mmol), was then reacted with BBr3 (1M in CH2Cl2, 0.05 ml, 0.05 mmol) in CH2Cl2 (2 ml) at −78° C. for 1 h, quenched with water, diluted with EtOAc, washed organic with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (5:95 MeOH—CH2Cl2) to yield the title compound as a white solid.

Workup

  1. customwas prepared (10 mg, 0.015 mmol)
  2. customquenched with water
  3. additiondiluted with EtOAc
  4. washwashed organic with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel (5:95 MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-1bf27a5b6b2f4300868506aeef3fb9e1
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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