Sodium hydride → HCID 19360176, compound

HRID 376877Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[C:9]([NH:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:21][CH2:22][CH2:23][C:24]1[C:28]2[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:27]=2[O:26][N:25]=1>CN(C=O)C>[Cl:1][C:2]1[C:10]2[C:9]([N:11]([CH2:21][CH2:22][CH2:23][C:24]3[C:28]4[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:27]=4[O:26][N:25]=3)[C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 4-chloro-3-[(4-pyridinyl)amino]benzo[b]thiophene (2.26 g, 8.67 mmole) in 25 mL DMF was added to a suspension of NaH (0.416 g of 60% in oil, 10.4 mmole, washed with heptane). To this mixture was added 3-(3-chloropropyl)-6-fluorobenzisoxazole (2.04 g, 9.53 mmole) and the reaction mixture was heated at 70° C. for 3 hours. The reaction mixture was quenched into water and extracted with ethyl acetate (3×). The organics were washed with water and dried (MgSO4). The compound was purified via flash chromatography (EtOAc) to give 2.8 g of a partially solidified oil. This was recrystallized from methanol/water to give 1.38 g of a white powder, mp: 135-136° C.

Workup

customThe reaction mixture was quenched into water
extractionextracted with ethyl acetate (3×)
washThe organics were washed with water
dry with materialdried (MgSO4)
customThe compound was purified via flash chromatography (EtOAc)
customto give 2.8 g of a partially solidified oil
customThis was recrystallized from methanol/water

Sources & evidence

ORD record: ord-c0807c5d74da48d28b86f1291f74ed5d
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06022880

Reaction notes

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