5-fluoropyridine-2-carboxylic Acid → (E)-Methyl 2-(5-fluoropicolinamido)-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate

HRID 1911042Notes

Reaction equation

HRID 1911042 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([CH3:16])[C:6]=2[CH:17]=1.[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:25](O)=[O:26])=[N:23][CH:24]=1>>[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[CH2:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([CH3:16])[C:6]=3[CH:17]=2)=[O:26])=[N:23][CH:24]=1

Participants

3

Reactant 2

HCID 27628765-fluoropyridine-2-carboxylic AcidHCID 86685426methyl 2-amino-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate

Product 1

HCID 86685434(E)-Methyl 2-(5-fluoropicolinamido)-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate

Procedure

In a manner similar to the procedure of step 3A, methyl 2-amino-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate from preparation J, step J1, was coupled with 5-fluoropicolinic acid to afford the titled compound of Step 43A. 1H NMR (500 HMz, chloroform-d) δ 9.82 (br. s., 1H), 8.48 (d, J=2.7 Hz, 1H), 8.36 (dd, J=8.7, 4.6 Hz, 1H), 7.73 (d, J=2.3 Hz, 1H), 7.66-7.59 (m, 2H), 7.22 (d, J=8.1 Hz, 1H), 3.83 (s, 3H), 2.57 (t, J=6.6 Hz, 2H), 2.45 (s, 3H), 2.17-2.10 (m, 4H).

Sources & evidence

ORD record
ord-b5d7b5a21297431e8039f6fbb5052638
Source dataset
uspto-grants-2013_12
Patent number
US08604024B2

Reaction notes

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