1-[3-(Benzyloxy)propyl]-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 3-[3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol

HRID 2279826Notes

Reaction equation

HRID 2279826 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16]([CH3:17])=[C:15]([B:18]2[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]2)[C:14]([CH3:27])=[N:13]1)C1C=CC=CC=1.C(OP(CC1C=CC(NC2N=C(NC3C=CC(C4C=C(C(OC)=O)N(CCCO)C=4)=NC=3C(=O)NC)C(C(F)(F)F)=CN=2)=C(OC)C=1)(O)=O)C>>[CH3:27][C:14]1[C:15]([B:18]2[O:22][C:21]([CH3:23])([CH3:24])[C:20]([CH3:25])([CH3:26])[O:19]2)=[C:16]([CH3:17])[N:12]([CH2:11][CH2:10][CH2:9][OH:8])[N:13]=1

Participants

3

Reactant 2

HCID 678121751-[3-(Benzyloxy)propyl]-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×HCID 86697760Methyl 4-[5-({2-[(4-{[ethoxy(hydroxy)phosphoryl]methyl}-2-methoxyphenyl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)-6-(methylcarbamoyl)pyridin-2-yl]-1-(3-hydroxypropyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 678139383-[3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-olYield 100.2%

Procedure

1-[3-(Benzyloxy)propyl]-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Compound 43C, 560 mg, 1.5 mmol) was hydrogenated using the procedure from Compound 38A to afford 421 mg of the desired title compound (99%). 1H NMR (400 MHz, CD3OD) δ 4.08 (t, J=7.1 Hz, 2H), 3.50 (t, J=6.1 Hz, 2H), 2.40 (s, 3H), 2.27 (s, 3H), 1.95 (t, J=6.7 Hz, 2H), 1.30 (s, 12H). MS (ESI): m/z=280.37 [M+H]+. UPLC: tR=1.29 min (UPLC-TOF: polar—2 min).

Sources & evidence

ORD record
ord-921d4005c0e24d59a574361f87517428
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

Loading…