Neopentyl alcohol → 3-((1S)-1-(tert-Butyldimethylsilyloxy)-7-fluoro-2,3-dihydro-1H-inden-4-yl)-2-(neopentyloxy)pyridine

HRID 237611Notes

Reaction equation

HRID 237611 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[H-].[Na+].[Si:9]([O:16][C@@H:17]1[C:25]2[C:20](=[C:21]([C:27]3[C:28](F)=[N:29][CH:30]=[CH:31][CH:32]=3)[CH:22]=[CH:23][C:24]=2[F:26])[CH2:19][CH2:18]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>CN1CCCC1=O>[Si:9]([O:16][C@@H:17]1[C:25]2[C:20](=[C:21]([C:27]3[C:28]([O:4][CH2:3][C:2]([CH3:6])([CH3:5])[CH3:1])=[N:29][CH:30]=[CH:31][CH:32]=3)[CH:22]=[CH:23][C:24]=2[F:26])[CH2:19][CH2:18]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 6404Neopentyl alcohol2×HCID 24758Sodium hydride2×HCID 866972813-((1S)-1-(tert-Butyldimethylsilyloxy)-7-fluoro-2,3-dihydro-1H-inden-4-yl)-2-fluoropyridine

Product 1

HCID 866972833-((1S)-1-(tert-Butyldimethylsilyloxy)-7-fluoro-2,3-dihydro-1H-inden-4-yl)-2-(neopentyloxy)pyridine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

2,2-Dimethylpropan-1-ol (59 mg) is dissolved at 0° C. in N-methylpyrrolidone (NMP, 2 mL), treated with NaH (27 mg, 55% dispersion in mineral oil) and stirred for 15 minutes. The mixture is warmed to room temperature, treated with a solution of 3-((1S)-1-(tert-butyldimethylsilyloxy)-7-fluoro-2,3-dihydro-1H-inden-4-yl)-2-fluoropyridine (200 mg) in N-methylpyrrolidone (NMP, 1 mL) and stirred for 12 hours at 75° C. 2,2-Dimethylpropan-1-ol (59 mg) and NaH (27 mg, 55% dispersion in mineral oil) are added and the mixture is stirred for 4 hours at 80° C. The mixture thus obtained is directly used in the next step.

Workup

  1. stirringstirred for 12 hours at 75° C
  2. stirringthe mixture is stirred for 4 hours at 80° C
  3. customThe mixture thus obtained

Sources & evidence

ORD record
ord-fc6888bce91745b2ad57e5f91334db4e
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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