Ethyl chloroformate → [6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol

HRID 2279112Notes

Reaction equation

HRID 2279112 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([C:31](O)=[O:32])[C:18]3[C:23]([CH3:24])=[N:22][N:21]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)[C:19]=3[N:20]=2)=[C:11]([F:34])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.ClC(OCC)=O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[C:19]3[N:21]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)[N:22]=[C:23]([CH3:24])[C:18]3=[C:17]([CH2:31][OH:32])[CH:16]=2)=[C:11]([F:34])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 866803216-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 118059348[6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanolYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C. to a solution of 3.00 g of 6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetra-hydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid in 50 ml of dry tetrahydrofurane were added 1.2 ml of Hünig's base, followed by slow addition of 0.7 ml of ethyl chlorformate. After 30 min at 0° C. the resulting suspension was filtered. Under argon atmosphere to the filtrate were added 290 mg of sodium borohydride and 15 ml of water. After 2 h at 0° C. sat. aqueous ammonium chloride solution was added. The layers were separated and the aqueous layer was extracted with methyl tert-butyl ether. The combined organic layers were dried over sodium sulphate, filtered and concentrated in vacuo. 1.60 g (55%) of the title compound were obtained.

Workup

  1. filtrationAfter 30 min at 0° C. the resulting suspension was filtered
  2. additionUnder argon atmosphere to the filtrate were added 290 mg of sodium borohydride and 15 ml of water
  3. additionAfter 2 h at 0° C. sat. aqueous ammonium chloride solution was added
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with methyl tert-butyl ether
  6. dry with materialThe combined organic layers were dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84e1a00c4563482199d1124eacc7474d
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

Loading…