Sodium Carbonate → HCID 86670055, compound

HRID 2044888Notes

Reaction equation

HRID 2044888 reaction equation
N([C@H]([C:6]1[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])C)=[N+]=[N-].N([C@H](C1C(Cl)=NC2C(C=1)=CC=CC=2F)C)=[N+]=[N-].C(=O)([O-])[O-].[Na+].[Na+].FC1C=C(B(O)O)C=CC=1>>[F:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[C:7]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[CH:6]=[CH:15]2

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 57707801HCID 57707801, compoundHCID 57708041HCID 57708041, compound

Product 1

HCID 86670055HCID 86670055, compound

Procedure

3-((S)-1-Azidoethyl)-8-fluoro-2-(3-fluorophenyl)quinoline was made according to Procedure BSL-1 using (S)-3-(1-azidoethyl)-2-chloro-8-fluoroquinoline (50 mg, 0.199 mmol), tetrakis triphenylphosphine palladium (0) (9 mg, 0.008 μmol, 0.04 eq), sodium carbonate (106 mg, 0.997 mmol, 5 eq), and 3-fluoro-phenylboronic acid (42 mg, 0.299 mmol, 1.5 eq). 34(S)-1-azidoethyl)-8-fluoro-2-(3-fluorophenyl)quinoline was obtained after purification. 1H NMR (400 MHz, CDCl3) δ ppm 8.39 (d, J=1.6 Hz, 1H), 7.71 (br d, J=8.2 Hz, 1H), 7.54 (td, J=7.8, 4.7 Hz, 1H), 7.52-7.42 (series of m, 2H), 7.35 (dt, J=7.8, 1.2 Hz), 7.31 (ddd, J=9.0, 2.4, 1.6 Hz, 1H), 7.20 (tdd, J=8.6, 2.7, 1.2 Hz, 1H), 4.94 (q, J=6.7 Hz, 1H), 1.56 (d, J=6.7 Hz, 3H). Mass Spectrum (ESI) m/e=310.9 (M+1).

Sources & evidence

ORD record
ord-f071da7f4b50478ebfecb3f27f3d72df
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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