Sodium Carbonate → HCID 86715483, compound

HRID 2284575Notes

Reaction equation

HRID 2284575 reaction equation
ClC1C(C2C=C3C(=CC=2)NN=C3)=CC=CN=1.[Cl:17][C:18]1[C:23]([C:24]2[CH:33]=[C:32]3[C:27]([CH:28]=[CH:29][N:30]=[CH:31]3)=[CH:26][CH:25]=2)=[CH:22][CH:21]=[CH:20][N:19]=1.BrC1C=C2C(C=CN=C2)=CC=1.ClC1C(B2OC(C)(C)C(C)(C)O2)=CC=CN=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[Cl:17][C:18]1[C:23]([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[N:30]=[CH:29][CH:28]=[CH:27]3)=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 120670602-Chloropyridine-3-boronic acid pinacol esterHCID 122574417-BromoisoquinolineHCID 867154695-(2-chloropyridin-3-yl)-1H-indazoleHCID 86715484HCID 86715484, compound

Product 1

HCID 86715483HCID 86715483, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Analogous to the preparation of 5-(2-chloropyridin-3-yl)-1H-indazole, 7-(2-chloropyridin-3-yl)isoquinoline was prepared by heating the mixture of 7-bromoisoquinoline (1.0 g, 4.8 mmol), 2-chloro-3-pyridine boronic acid pinacol ester (1.5 g, 6.20 mmol), Pd(PPh3)4 (330 mg, 0.28 mmol) and 2M aq.Na2CO3 (7 mL, 14 mmol) in 1,4-dioxane (40 mL). 6-(2-Chloropyridin-3-yl)quinoline was isolated as a white solid (820 mg, 70%) after the CH2Cl2 work-up and silica gel flash column purification. 1H NMR (DMSO-d6): δ 9.37 (s, 1H), 8.55 (d, 1H, J=5.8 Hz), 8.49 (dd, 1H, J=1.7 and 4.7 Hz), 8.23 (s, 1H), 8.07 (d, 1H, J=7.5 Hz), 8.02 (dd, 1H, J=1.7 and 7.6 Hz), 7.91-7.88 (m, 2H), 7.58 (dd, 1H, J=4.7 and 7.6 Hz).LCMS: rt 3.96 min (A), purity 95%, MS (m/e) 241 (MH+).

Workup

  1. customwas prepared
  2. temperatureby heating

Sources & evidence

ORD record
ord-a792acdc8f1f4b7c8107af9dd55ac431
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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