Sodium borohydride → 8-Bromo-6-fluoro-3-pyridin-3-yl-3,4-dihydro-2H-1,4-benzoxazin-5-amine

HRID 589134Notes

Reaction equation

HRID 589134 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([F:21])[C:7]([NH2:20])=[C:8]2[C:13]=1[O:12][CH2:11][C:10]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)=[N:9]2>C(O)C.O>[Br:3][C:4]1[CH:5]=[C:6]([F:21])[C:7]([NH2:20])=[C:8]2[C:13]=1[O:12][CH2:11][CH:10]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[NH:9]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 904091678-Bromo-6-fluoro-3-pyridin-3-yl-2H-1,4-benzoxazin-5-amine

Product 1

HCID 904097398-Bromo-6-fluoro-3-pyridin-3-yl-3,4-dihydro-2H-1,4-benzoxazin-5-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Sodium tetrahydroborate (44 mg, 1.2 mmol) was added to a solution of 8-bromo-6-fluoro-3-pyridin-3-yl-2H-1,4-benzoxazin-5-amine (190 mg, 0.58 mmol) in ethanol (4 mL) and water (1 mL), and heated at 90° C. for 15 minutes. The mixture was concentrated, diluted with water, and extracted with ethyl acetate. The organic solvents were evaporated to afford the product. LCMS calc. for C13H12BrFN3O (M+H)+: m/z=324.0. found: 324.0.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. customThe organic solvents were evaporated
  5. customto afford the product

Sources & evidence

ORD record
ord-0ab43aa6a7e444d1af7ac5815b1dcb9b
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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