(4-(Morpholin-4-yl)phenyl)boronic acid → HCID 57837448, compound

HRID 731740Notes

Reaction equation

HRID 731740 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:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1.C(C1C(C2C=C(N)C=CC=2)=C2C=CC=CN2N=1)(C)C>>[CH:11]([C:3]1[C:2]([C:23]2[CH:22]=[CH:21][C:20]([N:17]3[CH2:16][CH2:15][O:14][CH2:19][CH2:18]3)=[CH:25][CH:24]=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 2795359(4-(Morpholin-4-yl)phenyl)boronic acidHCID 57837481HCID 57837481, compoundHCID 57837525HCID 57837525, compound

Product 1

HCID 57837448HCID 57837448, compound

Procedure

2-Isopropyl-3-(4-morpholin-4-yl-phenyl)-pyrazolo[1,5-a]pyridine was prepared from 3-iodo-2-isopropyl-pyrazolo[1,5-a]pyridine and 4-morpholinophenylboronic acid following the method used in Step 3 of the synthesis of 3-(2-Isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-phenylamine (Example 59) (157 mg, 16%). 1H-NMR (250 MHz, DMSO-d6) δ 8.61 (d, J=6.3 Hz, 1H), 7.45 (d, J=9.0 Hz, 1H), 7.30 (d, J=7.0 Hz, 2H), 7.15-7.06 (m, 3H), 6.81 (t, J=6.5 Hz, 1H), 3.79-3.75 (m, 4H), 3.25 (sept, J=6.3 Hz, 1H), 3.22-3.15 (m, 4H), 1.27 (d, J=6.8 Hz, 6H); LC/MS 322.3 m/z (M+H+). Compound 1102.

Sources & evidence

ORD record
ord-760b7bf3bb7e40a5ab0130b6909e767d
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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