3-Ethynylpyridine → HCID 12011262, compound

HRID 593566Notes

Reaction equation

HRID 593566 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].[Cl:9][C:10]1[CH:16]=[C:15](I)[C:13]([NH2:14])=[CH:12][CH:11]=1>>[Cl:9][C:10]1[CH:11]=[C:12]2[C:13](=[CH:15][CH:16]=1)[NH:14][C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)=[CH:2]2

Participants

3

Reactant 2

HCID 1860033-EthynylpyridineHCID 27576154-Chloro-2-iodoaniline

Product 1

HCID 12011262HCID 12011262, compound

Procedure

3-Ethynylpyridine and 4-chloro-6-iodoaniline are processed according to the method described in Example 86 to give 5-chloro-2-pyridin-3-yl-1H-indole. 1H NMR (400 MHz, MeOD) δ ppm 6.96 (s, 1H), 7.14 (dd, J=8.6, 2.0 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 7.54 (dd, J=8.0, 4.9 Hz, 1H), 7.59 (d, J=2.0 Hz, 1H), 8.25 (dt, J=8.0, 1.9 Hz, 1H), 8.50 (d, J=4.5 Hz, 1H), 9.02 (s, 1H). HRMS (ESI) m/z 229.0522 [(M+H)+ Calcd for C13H10ClN2: 229.0533].

Sources & evidence

ORD record
ord-192bfda5eea3478b89563cb0fc934947
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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