(4-Aminophenyl)boronic acid--water (1/1) → HCID 57837454, compound

HRID 731739Notes

Reaction equation

HRID 731739 reaction equation
I[C:2]1[C:3]([CH:11]([CH3:13])[CH3:12])=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.O.[NH2:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(C1C(C2C=C(N)C=CC=2)=C2C=CC=CN2N=1)(C)C>>[CH:11]([C:3]1[C:2]([C:19]2[CH:20]=[CH:21][C:16]([NH2:15])=[CH:17][CH:18]=2)=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)([CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 57356985(4-Aminophenyl)boronic acid--water (1/1)HCID 57837481HCID 57837481, compoundHCID 57837525HCID 57837525, compound

Product 1

HCID 57837454HCID 57837454, compound

Procedure

4-(2-Isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-phenylamine was prepared from 3-iodo-2-isopropyl-pyrazolo[1,5-a]pyridine and 4-aminophenylboronic acid monohydrate following the method used in Step 3 of the synthesis of 3-(2-Isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-phenylamine as in Example 59 above (134 mg, 18%). 1H-NMR (250 MHz, DMSO-d6) δ 8.58 (d, J=7.0 Hz, 1H), 7.42 (d, J=7.8 Hz, 1H), 7.14-7.04 (m, 3H), 6.77 (t, J=7.0 Hz, 1H), 6.67 (d, J=8.5 Hz, 2H), 5.15 (s, 2H), 3.23 (sept, J=6.8 Hz, 1H), 1.26 (d, J=7.0 Hz, 6H). LC/MS 252.3 m/z (M+H+). Compound 1101.

Sources & evidence

ORD record
ord-5ec26c24f2b74f3fb6c41e4d68124f31
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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