Sodium borohydride → HCID 23653201, compound

HRID 1094515Notes

Reaction equation

HRID 1094515 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[C:10]([O:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[C:23](=[O:36])[NH:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:26]=3)[CH:14]=2)[CH:9]=[CH:8][N:7]=1)=O)C.[BH4-].[Na+]>C(O)(C)(C)C>[F:31][C:28]1[CH:29]=[CH:30][C:25]([NH:24][C:23]([C:19]2[C:20]3[C:15](=[CH:14][C:13]([O:12][C:10]4[CH:9]=[CH:8][N:7]=[C:6]([CH2:4][OH:3])[N:11]=4)=[CH:22][CH:21]=3)[CH:16]=[CH:17][CH:18]=2)=[O:36])=[CH:26][C:27]=1[C:32]([F:34])([F:33])[F:35]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23653200HCID 23653200, compound

Product 1

HCID 23653201HCID 23653201, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 523 mg (1.048 mMol) 4-[5-(4-fluoro-3-trifluoromethyl-phenylcarbamoyl)-naphthalen-2-yloxy]-pyrimidine-2-carboxylic acid ethyl ester in 13.8 ml tert-butanol, 119 mg (3.14 mMol) NaBH4 are added. This mixture is stirred for 2 h at 70° C. and then concentrated in vacuo. The residue is diluted with water and EtOAc, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed with brine, dried (Na2SO4) and concentrated. Chromatography [Combi Flash; CH2Cl2/(CH2Cl2/tertBuOH 1:1) 99:1→83:17] and trituration from DIPE gives the title compound: Anal. (+0.3H2O+0.4 DIPE): C, H, N, F; MS: [M+1]+=458; TLC (CH2Cl2/acetone 9:1): Rf=0.44.

Workup

  1. additionare added
  2. concentrationconcentrated in vacuo
  3. additionThe residue is diluted with water and EtOAc
  4. customthe aq. phase separated off
  5. extractionextracted twice with EtOAc
  6. washThe organic layers are washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f46b2230edb248be83168d9dc6a36c0c
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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