Ammonium Chloride → HCID 117778576, compound

HRID 2206582Notes

Reaction equation

[CH3:1][C:2]1[N:10]([CH:11]([CH3:14])[CH:12]=[O:13])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[Si]([C:26]([F:29])([F:28])[F:27])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-]>C1COCC1>[CH3:1][C:2]1[N:10]([CH:11]([CH:12]([OH:13])[C:26]([F:29])([F:28])[F:27])[CH3:14])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 2-methyl-1-(1-oxopropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (100 mg, 0.35 mmol) in dry THF (2 ml) was added a solution of TMS-CF3 (0.02 ml, 1M in THF) and the reaction mixture was cooled to 0° C. under Ar, Added TBAF (73.97 mg, 0.52 mmol), via drop-wise addition and stirred for 30 min at 0° C. A solution of saturated NH4Cl was added and most of the solvent was stripped on the ratary evaporator. The reminder was taken up EtOAc and H2O and transferred to a separatory funnel. The mixture was shaken and the organic layer was separated, dried over Na2SO4, and evaporated under reduced pressure to give tert-butyl 2-methyl-1-(4,4,4-trifluoro-3-hydroxybutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate as a white crystal (40 mg, yield 32%).

Workup

additionvia drop-wise addition
customwas stripped on the ratary evaporator
customtransferred to a separatory funnel
stirringThe mixture was shaken
customthe organic layer was separated
dry with materialdried over Na2SO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-855536ebccc8426b8f5e1d5ed0bd2a1f
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371331B2

Reaction notes

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