1-Cyclohexenylboronic acid → HCID 59128594, compound

HRID 1992005Notes

Reaction equation

HRID 1992005 reaction equation
[C:1]1(B(O)O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.Br[C:11]1[CH:16]=[C:15]([C:17]2[CH2:18][CH2:19][N:20]([O:23][CH3:24])[CH2:21][CH:22]=2)[CH:14]=[CH:13][C:12]=1[NH2:25]>>[C:1]1([C:13]2[CH:14]=[C:15]([CH:17]3[CH2:22][CH2:21][N:20]([O:23][CH3:24])[CH2:19][CH2:18]3)[CH:16]=[CH:11][C:12]=2[NH2:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

3

Reactant 2

HCID 38629021-Cyclohexenylboronic acidHCID 68450954HCID 68450954, compound

Product 1

HCID 59128594HCID 59128594, compoundYield 76.8%

Procedure

The title compound was then prepared according to Suzuki coupling procedure of Example 12, step (d) using cyclohex-1-enyl boronic acid (27.9 mg, 1.00 mmol) and 2-bromo-4-(1-methoxy-1,2,3,6-tetrahydro-pyridin-4-yl)-phenylamine (as prepared above, 44 mg, 0.15 mmol) and chromatographed on silica (20-50% EtOAc/hexanes) afforded 2-cyclohex-1-enyl-4-(1-methoxy-piperidin-4-yl)-phenylamine (33 mg, 74%). Mass spectrum, (ESI, m/z): Calcd. for C18H26N2O, 287.2 (M+H), found 286.8.

Workup

  1. customchromatographed on silica (20-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-37e1bbf586c54b319d311f7ff38a82fe
Source dataset
uspto-grants-2010_01
Patent number
US07645755B2

Reaction notes

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