Dichloromethane → HCID 86593499, compound

HRID 1178622Notes

Reaction equation

HRID 1178622 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[CH:11][S:12][C:3]=12.[C:13]([O:17][C:18]([CH:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].Cl[CH2:41]Cl>>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[C:11](/[CH:41]=[CH:20]/[C:18]([O:17][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19])[S:12][C:3]=12

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 118164017-Chlorothieno[3,2-b]pyridine-6-carbonitrile

Product 1

HCID 86593499HCID 86593499, compound

Procedure

To a solution of 7-chlorothieno[3,2-b]pyridine-6-carbonitrile (100 mg, 0.45 mmol) in 5 mL of dichloromethane is added, in portions, (tert-butoxycarbonylmethylene)triphenylphosphorane (0.645 mL, 1.29 mmol). After stirring for 2.5 hours, the reaction mixture is allowed to stand at room temperature overnight. The mixture is concentrated to ½ its volume and is purified by flash column chromatography eluting with dichloromethane to provide 126 mg of tert-butyl (2E)-3-(7-chloro-6-cyanothieno[3,2-b]pyridin-2-yl)prop-2-enoate as a white solid, mp 193–194° C.; 1H NMR (CDCl3) δ 1.55 (s, 9H), 6.46 (d, J=16 Hz, 1H), 7.26 (s, 1H), 7.70 (s, 1H), 7.77 (d, J=16 Hz, 1H), 8.84 (s, 1H); MS 321.1, 323.2 (M+H)+

Workup

  1. waitto stand at room temperature overnight
  2. concentrationThe mixture is concentrated
  3. customis purified by flash column chromatography
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-f15f084569f74617adf405d9aafb1c0f
Source dataset
uspto-grants-2007_10
Patent number
US07276519B2

Reaction notes

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