Sodium borohydride → HCID 54766252, compound

HRID 1503290Notes

Reaction equation

HRID 1503290 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][C:31]=1[C:32]([F:35])([F:34])[F:33])[O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([C:24](=[O:28])[C:25]([NH2:27])=[O:26])=[CH:16]2)=[CH:11][CH:10]=1)#[N:4]>CCO.C1COCC1>[C:3]([C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][C:31]=1[C:32]([F:35])([F:33])[F:34])[O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]([OH:28])[C:25]([NH2:27])=[O:26])=[CH:16]2)=[CH:13][CH:14]=1)#[N:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54766251HCID 54766251, compound

Product 1

HCID 54766252HCID 54766252, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

NaBH4 (40 mg) was added to a solution of compound 59 in EtOH/THF (2 mL/2 mL) at room temperature, and the mixture was shaken at room temperature for 3 hours. The reaction was quenched with water, extracted with EtOAc (30 mL), concentrated, and purified by column (CHCl3/MeOH 7/1) to give compound 60 as a white solid (70 mg, 70%): 1H-NMR (400 MHz, CD3OD): δ 7.92 (d, 1H, 8.8 Hz), 7.87 (d, 1H, 7.9 Hz), 7.66-7.69 (m, 3H), 7.53-7.56 (m, 2H), 7.45-7.48 (m, 1H), 7.35-7.38 (m, 1H), 7.15-7.25 (m, 2H), 5.41 (br, 1H); LC/MS: m/z=474.3 [M+Na]+ (Calc: 451.4).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc (30 mL)
  3. concentrationconcentrated
  4. custompurified by column (CHCl3/MeOH 7/1)

Sources & evidence

ORD record
ord-16fd36f3795744de91282ce049a650f0
Source dataset
uspto-grants-2015_12
Patent number
US09212139B2

Reaction notes

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