Sodium borohydride → HCID 9883654, compound

HRID 2183596Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11]3[N:12]4[CH2:20][CH2:19][N:18]=[C:13]4[S:14][C:15]=3[CH:16]=[O:17])[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>>[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11]3[N:12]4[CH2:20][CH2:19][N:18]=[C:13]4[S:14][C:15]=3[CH2:16][OH:17])[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 22473919HCID 22473919, compound

Product 1

HCID 9883654HCID 9883654, compound

Procedure

This Example was performed in a similar manner to Example 3. 3-(4-Chlorobenzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]-thiazole hydrobromide (1.5 g, see Example 1) was basified to give 3-(4-chlorobenzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole which was brominated to give 2-bromo-3-(4-chlorobenzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (1.13 g) as a pale yellow solid, m.p. 227-229° C. This was reacted with ethylmagnesium chloride (2.0 M solution in ether; 3.75 ml) in tetrahydrofuran (20 ml) followed by dimethylformamide (0.83 ml) to give 3-(4-chlorobenzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole-2-carboxaldehyde. (0.65 g) as a red-brown solid after flash chromatography. This aldehyde was reduced with sodium borohydride (0.13 g) to give [3-(4-chlorobenzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazol-2-yl]methanol (0.22 g) as a yellow solid, m.p. 170-172° C.

Sources & evidence

ORD record: ord-decd170478584cafb5ab88754253f5df
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900216B2

Reaction notes

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