2-(Trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylate → 2-(Trimethylsilyl)ethyl 4-[4-(1-acetyl-4-hydroxypiperidin-4-yl)phenyl]isoquinoline-6-carboxylate

HRID 1959950Notes

Reaction equation

HRID 1959950 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[CH:15]=2)[CH:10]=[N:9][CH:8]=1)(=O)=O.[C:28]([N:31]1[CH2:36][CH2:35][C:34]([C:38]2[CH:43]=[CH:42][C:41](B3OC(C)(C)C(C)(C)O3)=[CH:40][CH:39]=2)([OH:37])[CH2:33][CH2:32]1)(=[O:30])[CH3:29]>>[C:28]([N:31]1[CH2:36][CH2:35][C:34]([C:38]2[CH:43]=[CH:42][C:41]([C:7]3[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[CH:15]=4)[CH:10]=[N:9][CH:8]=3)=[CH:40][CH:39]=2)([OH:37])[CH2:33][CH2:32]1)(=[O:30])[CH3:29]

Participants

3

Reactant 2

HCID 584957602-(Trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylateHCID 667305831-Acetyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperidin-4-ol

Product 1

HCID 667303932-(Trimethylsilyl)ethyl 4-[4-(1-acetyl-4-hydroxypiperidin-4-yl)phenyl]isoquinoline-6-carboxylateYield 100%

Procedure

Using 2-(trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylate (800 mg, 1.90 mmol) and 1-acetyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperidin-4-ol (983 mg, 2.85 mmol) synthesized in Reference Example 10, the desired title compound (931 mg, yield 100%) was obtained by the same method as in Reference Example 4 (4a).

Workup

  1. customsynthesized in Reference Example 10

Sources & evidence

ORD record
ord-18a1d1fb5eaf4159b96f4c81704379d8
Source dataset
uspto-grants-2013_04
Patent number
US08410273B2

Reaction notes

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