HCID 57494746, compound → HCID 57444749, compound

HRID 861161Notes

Reaction equation

HRID 861161 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([CH:18]=[O:19])=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([Cl:16])[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:20]([Mg]Br)#[CH:21]>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([CH:18]([OH:19])[C:20]#[CH:21])=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([Cl:16])[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 57494746HCID 57494746, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 57444749HCID 57444749, compoundYield 68%

Procedure

In a similar manner as described in Example 46 from 2-(3-bromophenyl)-7-chloropyrazolo[1,5-a]pyridine-3-carbaldehyde (1.0 g, 2.9 mmol) and ethynylmagnesium bromide (6.4 mL, 0.5 M in tetrahydrofuran, 3.2 mmol) at 0 ° C., was obtained 1-[2-(3-bromophenyl)-7-chloropyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-ol (0.68 g, 68%) as a white solid. 1H NMR (DMSO-d6): δ 8.04 (m, 2 H), 7.87 (d, 1 H), 7.67 (d, 1 H), 7.49 (t, 1 H), 7.38–7.29 (m, 2 H), 6.27 (bs, 1 H), 5.69 (s, 1 H), 3.49 (d, 1 H).

Sources & evidence

ORD record
ord-3f30da6007cb47d2b0002e7b08b01df0
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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