2-Methylindole → HCID 16659713, compound

HRID 2264686Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.I[C:11]1[CH:16]=[CH:15][C:14](O)=CC=1.[CH3:18][C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2>>[Cl:9][C:4]1[CH:3]=[C:2]([N:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:27]=[C:19]2[CH3:18])[CH:7]=[CH:6][C:5]=1[O:8][CH2:26][CH2:27][CH2:19][N:20]1[CH2:14][CH2:15][CH2:16][CH2:11]1

Participants

Reactant 3

HCID 72242-Methylindole

HCID 108944-Iodophenol

HCID 198594-Bromo-2-chlorophenol

Product 1

HCID 16659713HCID 16659713, compound

Procedure

1-[3-Chloro-4-(3-pyrrolidin-1-ylpropoxy)phenyl]-2-methyl-1H-indole was synthesized by a method analogous to that used for Example 4, using 4-bromo-2-chlorophenol in the first step rather than 4-iodophenol and 2-methylindole in the final step. LC-MS (C22H25ClN2O calc'd 368) m/z 369, 371 (M+H); 1H NMR (300 MHz, CDCl3) d 7.58-7.54 (m, 1H), 7.37 (d, J=2.4 Hz, 1H), 7.20 (dd, J=8.7 Hz, 2.7 Hz, 1H), 7.11-7.02 (m, 4H), 6.38 (s, 1H), 4.19 (t, J=6.3 Hz, 2H), 2.88 (t, J=7.2 Hz, 2H), 2.77 (m, 4H), 2.24-2.15 (m, 2H), 1.91-1.87 (m, 4H).

Sources & evidence

ORD record: ord-69c536b0c9f34dbf9c91282af637e4a4
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855224B2

Reaction notes

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