Sodium borohydride → HCID 136242911, compound

HRID 1775207Notes

Reaction equation

HRID 1775207 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:20](=[O:21])[NH:19][N:18]=[C:7]3[CH2:8][C:9]([CH3:17])([CH3:16])[C:10](=[O:15])[C:11]4[NH:12][C:13]([CH:14]=1)=[C:5]2[C:6]=43.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:20](=[O:21])[NH:19][N:18]=[C:7]3[CH2:8][C:9]([CH3:17])([CH3:16])[CH:10]([OH:15])[C:11]4[NH:12][C:13]([CH:14]=1)=[C:5]2[C:6]=43

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178423527HCID 178423527, compound

Product 1

HCID 136242911HCID 136242911, compoundYield 9.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-fluoro-2,2-dimethyl-2,3-dihydro-[1,2]diazepino[3,4,5,6-def]carbazole-1,6(5H, 10H)-dione (50 mg, 0.18 mmol) in 10 mL of MeOH, was added NaBH4 (0.18 mmol) at 0° C. The mixture was stirred for additional 30 min. The solution was poured into ice water, and extracted with EtOAc (5mL×3). The organic layers were combined, washed with H2O (5mL×3) and brine (5mL×3), dried over Na2SO4, and filtered. The filtrate was concentrated, and the residue was chromatographed to give the crude product which was then purified on Pre-HPLC to give the product (5 mg) as a yellow solid. 1H NMR (DMSO-d6) δ 11.9 (s, 1H), 10.1 (s, 1H), 7.23 (dd, 1H, J=9.2, 2.0 Hz), 7.17 (dd, 1H, J=10.8, 2.4 Hz), 5.68 (d, 1H, J=6.0 Hz), 5.49 (d, 1H, J=6.0 Hz), 2.31 (s, 2H), 1.00 (s, 3H), and 0.88 (s, 3H). MS (ESI) m/e [M+1]+ 288.

Workup

  1. extractionextracted with EtOAc (5mL×3)
  2. washwashed with H2O (5mL×3) and brine (5mL×3)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was chromatographed
  7. customto give the crude product which
  8. customwas then purified on Pre-HPLC

Sources & evidence

ORD record
ord-d9f639a6d88c47f0be515c3d5f76f626
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

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