6-Bromoquinoline → HCID 86696267, compound

HRID 2175146Notes

Reaction equation

HRID 2175146 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH3:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:19]=[CH:20][C:21]3[N:22]([C:24]([SH:27])=[N:25][N:26]=3)[CH:23]=2)[CH:15]=[N:14]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CCN(C(C)C)C(C)C>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:19]=[CH:20][C:21]3[N:22]([C:24]([S:27][C:2]4[CH:3]=[C:4]5[C:9](=[CH:10][CH:11]=4)[N:8]=[CH:7][CH:6]=[CH:5]5)=[N:25][N:26]=3)[CH:23]=2)[CH:15]=[N:14]1

Participants

7

Reactant 4

HCID 792436-BromoquinolineHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178480033HCID 178480033, compound

Product 1

HCID 86696267HCID 86696267, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromoquinoline (72.0 mg, 0.346 mmol), Intermediate E (80 mg, 0.346 mmol), Pd2(dba)3 (31.7 mg, 0.035 mmol), xantphos (40.0 mg, 0.069 mmol) and DIPEA (0.242 ml, 1.384 mmol) in DMF (10 ml) was bubbled with N2 for 15 min. The reaction was stirred at 100° C. for 2 h under MW radiation. The mixture was concentrated and the residue obtained was purified by silica gel chromatography eluted with DCM/MeOH (from 100% to 90%) to afford the title compound as yellow solid (63 mg, 45.7% yield). 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.65 (d, 1H), 8.59 (s, 1H), 8.28 (m, 2H), 7.98 (m, 3H), 7.89 (s, 1H), 7.81 (d, 1H), 7.59 (d, 1H), 7.50 (m, 1H), 3.84 (s, 3H). LCMS (method B): [M+H]+=359, tR=2.0 min.

Workup

  1. customwas bubbled with N2 for 15 min
  2. concentrationThe mixture was concentrated
  3. customthe residue obtained
  4. customwas purified by silica gel chromatography
  5. washeluted with DCM/MeOH (from 100% to 90%)

Sources & evidence

ORD record
ord-10986fa92bbc44c88efd6fad637778e4
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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