Lithium borohydride → HCID 131732302, compound

HRID 1424855Notes

Reaction equation

HRID 1424855 reaction equation
[Li+].[BH4-].[Br:3][C:4]1[CH:13]=[CH:12][C:11]([N:14]([C:19]2[C:38]([CH:39]3[CH2:41][CH2:40]3)=[CH:37][C:22]3[C:23]([C:33](=[O:36])[NH:34][CH3:35])=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[O:25][C:21]=3[CH:20]=2)[S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][C:5]=1[C:6](OC)=[O:7]>C1COCC1.CO>[Br:3][C:4]1[CH:13]=[CH:12][C:11]([N:14]([C:19]2[C:38]([CH:39]3[CH2:41][CH2:40]3)=[CH:37][C:22]3[C:23]([C:33]([NH:34][CH3:35])=[O:36])=[C:24]([C:26]4[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=4)[O:25][C:21]=3[CH:20]=2)[S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][C:5]=1[CH2:6][OH:7]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 131732301HCID 131732301, compound

Product 1

HCID 131732302HCID 131732302, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

LiBH4 (1.593 mL, 3.19 mmol) solution (2M in THF) was added dropwise to a solution of methyl 2-bromo-5-(N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)benzoate (0.76 g, 1.062 mmol) in tetrahydrofuran (6.0 mL) and methanol (0.600 mL) at 0° C. under N2. The mixture was stirred for 3 hours at the same temperature. It was quenched with 1M NaOH and then partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×). The organic phase was washed with brine, dried over Na2SO4. It was concentrated to dryness to give the crude product (>99%) as tan foam which was used for the next step without further purification. LCMS (m/z, ES+)=587 (M+H+).

Workup

  1. customIt was quenched with 1M NaOH
  2. custompartitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc (2×)
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationIt was concentrated to dryness

Sources & evidence

ORD record
ord-17a3658fa11e454fa89ecbd0e3ee55f6
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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