Ethylacetate methanol → HCID 67972428, compound

HRID 41885Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]4[CH2:19][CH2:20][CH2:21][C:14]=34)=[CH:11][N:10]([CH3:22])[N:9]=2)=[CH:4][CH:3]=1.CC[O:25]C(C)=O.CO>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N+:16]([O-:25])=[C:15]4[CH2:19][CH2:20][CH2:21][C:14]=34)=[CH:11][N:10]([CH3:22])[N:9]=2)=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 21584119Ethylacetate methanol

HCID 67972067HCID 67972067, compound

Product 1

HCID 67972428HCID 67972428, compound

Procedure

4-[3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-6,7-dihydro-5H-cyclopenta[b]pyridine was converted to the N-oxide following the general procedure described in Example 1, step 9. Silica gel chromatography using a 9:1 to 4:1 mixture of EtOAc/MeOH afforded 54% of Ex 24-Step 1 product as a yellow solid: LCMS m/z 310.5 (M+1); 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J=6.6, 1H), 7.45 (s, 1H), 7.35 (dd, J=8.9, 5.4, 2H), 7.00 (dd, J=8.7, 8.7, 2H), 6.89 (d, J=6.6, 1H), 3.97 (s, 3H), 3.17 (t, J=7.6, 2H), 2.67 (t, J=7.6, 2H), 2.02-2.09 (m, 2H).

Workup

customafforded 54% of Ex 24-Step 1 product as a yellow solid

Sources & evidence

ORD record: ord-5139ca1ad47f4ef2b6f19ffd65b9caf4
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536164B2

Reaction notes

Loading…