Pyridine → HCID 117668198, compound

HRID 1052977Notes

Reaction equation

HRID 1052977 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]3(O)[C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)=[C:5]([CH3:23])[O:4][N:3]=1.N1C=CC=CC=1.O=S(Cl)[Cl:32]>C(Cl)Cl>[Cl:32][C:10]1([C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:23])[CH:8]=2)[NH:12][C:11]1=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 86295676HCID 86295676, compound

Product 1

HCID 117668198HCID 117668198, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(3,5-dimethylisoxazol-4-yl)-3-hydroxy-3-(thiophen-3-yl)indolin-2-one (500 mg, 1.53 mmol) in CH2Cl2 (75.0 mL) was added pyridine (1.21 g, 15.3 mmol) followed by SOCl2 (728 mg, 6.12 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 2 h and the mixture was evaporated in vacuum to give crude product, which was used for the next step without further purification.

Workup

  1. customthe mixture was evaporated in vacuum
  2. customto give crude product, which
  3. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-b9fb0d60474643b58f797353d1d425f0
Source dataset
uspto-grants-2016_07
Patent number
US09393232B2

Reaction notes

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