Potassium cyclopropyltrifluoroborate → 5-Cyclopropyl-7-methyl-1-tosyl-1H-indole-4-carbaldehyde

HRID 2173972Notes

Reaction equation

HRID 2173972 reaction equation
Cl[C:2]1[C:3]([CH2:22][O:23]C2CCCCO2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[CH:30]1([B-](F)(F)F)[CH2:32][CH2:31]1.[K+]>>[CH:30]1([C:2]2[CH:10]=[C:9]([CH3:11])[C:8]3[N:7]([S:12]([C:15]4[CH:16]=[CH:17][C:18]([CH3:19])=[CH:20][CH:21]=4)(=[O:13])=[O:14])[CH:6]=[CH:5][C:4]=3[C:3]=2[CH:22]=[O:23])[CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 23697338Potassium cyclopropyltrifluoroborateHCID 867015385-chloro-7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indole

Product 1

HCID 721918285-Cyclopropyl-7-methyl-1-tosyl-1H-indole-4-carbaldehyde

Procedure

The title compound was synthesized starting from 5-chloro-7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indole as described in Example 48-A to 48-C using potassium cyclopropyltrifluoroborate in place of potassium ethylrifluoroborate in Example 48-A. MS (ESI+) m/z 354.2 (M+H).

Sources & evidence

ORD record
ord-8a47e95cc66a47f6aca14675a012506d
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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