Sodium cyanoborohydride → HCID 25054501, compound

HRID 2423182Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]2[C:20]([CH3:25])=[N:21][CH2:22][CH2:23][O:24][C:3]=12.[BH3-]C#N.[Na+]>CCO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:13])=[C:4]2[CH:20]([CH3:25])[NH:21][CH2:22][CH2:23][O:24][C:3]=12

Participants

Conditions

Temperature: 50 °C

Procedure

6-Fluoro-1-methyl-8-(phenylsulfonyl)-3,8-dihydro-4H-[1,4]oxazepino[6,7-e]indole (Intermediate 31, 0.010 g, 0.028 mmol) was dissolved in EtOH (2 mL) and NaCNBH3 (3.5 mg, 0.056 mmol) was added. The reaction mixture was heated at 50° C. for 1 hour. The reaction was quenched by addition of water and the solvent was removed under reduced pressure. The crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (1.2 mg). MS m/z 361 [M+H]+.

Workup

customThe reaction was quenched by addition of water
customthe solvent was removed under reduced pressure
customThe crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN)

Sources & evidence

ORD record: ord-4edb8146260d41b4a17b5a000f7c635a
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

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