Sodium ethoxide → HCID 86596770, compound

HRID 861163Notes

Reaction equation

HRID 861163 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([C:18](=O)[C:19]#[CH:20])=[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.S(O)(O)(=O)=O.[CH:27]1([NH:30][C:31]([NH2:33])=[NH:32])[CH2:29][CH2:28]1.[O-]CC.[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([C:18]3[CH:19]=[CH:20][N:33]=[C:31]([NH:30][CH:27]4[CH2:29][CH2:28]4)[N:32]=3)=[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

4

Reactant 3

HCID 2723922Sodium ethoxideHCID 57444750HCID 57444750, compoundHCID 178512454HCID 178512454, compound

Product 1

HCID 86596770HCID 86596770, compoundYield 39%

Procedure

In a similar manner as described in Example 46 from 1-[2-(3-bromophenyl)-7-chloropyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (0.45 g, 1.25 mmol), N-cyclopropylguanidine sulfate and sodium ethoxide (0.61 mL, 21 wt % in ethanol, 1.6 mmol) at room temperature was obtained 4-[2-(3-bromophenyl)-7-chloropyrazolo[1,5-a]pyridin-3-yl]-N-cyclopropyl-2-pyrimidinamine (0.21 g, 39%) as a pale yellow solid. 1H NMR (CDCl3): δ 8.57 (d, 1 H), 8.12 (d, 1 H), 7.86 (t, 1 H), 7.57 (m, 2 H), 7.28 (m, 2 H), 7.06 (d, 1 H), 6.37 (d, 1 H), 5.38 (bs, 1 H), 2.84 (m, 1 H), 0.88 (m, 2 H), 0.63 (m, 2 H); MS m/z 440 (M+1).

Sources & evidence

ORD record
ord-b9c0b2a50fbc41f38922cca5900428ff
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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