Cesium carbonate → HCID 60209928, compound

HRID 1497334Notes

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[N:13][CH:14]=1.[OH-].[Na+].[F:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[C:27]([C:30]([O:32]C)=[O:31])[CH:26]=[C:25]2B1OC(C)(C)C(C)(C)O1>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.CO.O>[F:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[C:27]([C:30]([OH:32])=[O:31])[CH:26]=[C:25]2[CH2:8][C:9]1[CH:14]=[N:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of the above compound (S1) (130 mg, 0.393 mmol) and Pd(dppf)Cl2-CH2Cl2 adduct (32.1 mg, 0.039 mmol) and Cs2CO3 (384 mg, 1.178 mmol) in a microwave tube was add a solution of 5-(chloromethyl)-2-methoxypyridine (124 mg, 0.785 mmol) in THF (3 mL) followed by water (0.3 mL). The mixture was heated at 100° C. for 1 h. LC-MS indicated the product (S2) existed as a mixture of both desired ester (ES-MS [M+1]+: 327.2) and hydrolyzed acid (ES-MS [M+1]+: 313.2). The mixture was transferred to a 100 mL round-bottom flask followed by adding MeOH (11 mL) and NaOH (1 N in H2O, 4.5 mL). The reaction was stirred at room temperature for 1 h to allow the complete conversion of the remaining ester to the acid. The solvents were removed to provide crude 8-fluoro-4-[(6-methoxypyridin-3-yl)methyl]quinoline-2-carboxylic acid (S3). ES-MS [M+1]+: 313.2.

Workup

customThe mixture was transferred to a 100 mL round-bottom flask
customThe solvents were removed

Sources & evidence

ORD record: ord-576d584dd29e4b89869ba988f0fa4aab
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199939B2

Reaction notes

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