Lithium Chloride → HCID 68709474, compound

HRID 222122Notes

Reaction equation

HRID 222122 reaction equation
Br.[CH2:2]([O:4][C:5]([C:7]1[C:19]2[CH2:18][CH2:17][C:16]3[CH:15]=[N:14][CH:13]=[CH:12][C:11]=3[C:10]=2[NH:9][C:8]=1Br)=[O:6])[CH3:3].[C:21]1([CH3:30])[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.[Li+].[Cl-]>C1(C)C=CC=CC=1.C(O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:2]([O:4][C:5]([C:7]1[C:19]2[CH2:18][CH2:17][C:16]3[CH:15]=[N:14][CH:13]=[CH:12][C:11]=3[C:10]=2[NH:9][C:8]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH3:30])=[O:6])[CH3:3]

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 27332672-Methylphenyl boronic acidHCID 68705832HCID 68705832, compound

Product 1

HCID 68709474HCID 68709474, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of 2-bromo-4,5-dihydro-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylic acid ethyl ester F1 (0.497 mmol) in toluene (4 mL) and ethanol (4 mL), o -tolylboronic acid (0.75 mmol), LiCl (1.49 mmol), Na2CO3.10H2O (1.74 mmol) and (PPh3)2PdCl2 (3.5 mg) were added. The mixture was heated at 150° C. for 15 min with microwave irradiation then evaporated to dryness. Chromatography on silica gel (eluant: DCM/MeOH 95:5) afforded the title compound (85% yield). ESI (+) MS: m/z 333 (MH+). 1H NMR: 1.03 (d, J=7.07, 3H), 2.18 (s, 3H), 2.93 (t, J=7.40, 2H), 3.03 (t, J=7.30, 2H), 4.00 (q, J=7.07, 2H), 7.22-7.39 (m, 4H), 7.45 (d, J=5.12, 1H), 8.34 (d, J=5.00, 1H), 8.36 (s, 1H), 12.18 (bs, 1H). Employing the same methodology but using phenylboronic acid the following compound was prepared:

Workup

  1. additionwere added
  2. customthen evaporated to dryness

Sources & evidence

ORD record
ord-0ee8eea0cd0c4453a1bad5102f86e61b
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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