5-Methoxy-1H-indole-2-carbaldehyde → D-64131

HRID 11141

Reaction equation

HRID 11141 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH:12]=[O:13])=[CH:6]2.[C:14]1([Mg]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13])=[CH:6]2

Participants

3

Reactant 2

HCID 8264565-Methoxy-1H-indole-2-carbaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 3921152D-64131Yield 91%

Procedure

Reaction of 5-methoxy-1H-indole-2-carbaldehyde with phenylmagnesium bromide using the procedure described in example 404 gave (805) (91%), mp 159–161° C. 1H NMR δ [(CD3)2SO] 11.86 (s, 1H), 7.94–7.91 (m, 2H), 7.71–7.66 (m, 1H), 7.61–7.57 (m, 2H), 7.42 (d, J=8.9 Hz, 1H), 7.16 (d, J=2.4 Hz, 1H), 7.03 (s, 1H), 6.99 (dd, J=8.9, 2.4 Hz, 1H), 3.77 (s, 3H). Found: C, 76.28; H, 5.21; N, 5.42. C16H13NO2 requires: C, 76.48; H, 5.21; N, 5.57.

Sources & evidence

ORD record
ord-9bcf57638ec4461986b37612b541e68c
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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