Sodium Carbonate → 5-[2-(4-Trifluoromethyl-phenyl)-vinyl]1H-pyrrolo[2,3-b]pyridine

HRID 1994204Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[Cl-].[Li+].[F:13][C:14]([F:27])([F:26])[C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/B(O)O)=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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.CCO>[F:13][C:14]([F:26])([F:27])[C:15]1[CH:16]=[CH:17][C:18]([CH:21]=[CH:22][C:2]2[CH:3]=[C:4]3[CH:10]=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 105 °C

Procedure

To a solution of bromide 27 (76 mg, 0.39 mmol), lithium chloride (49 mg, 1.16 mmol), trans-2[4-(trifluoromethyl)-phenyl]vinyl boronic acid (125 mg, 0.58 mmol) in a mixture of toluene (3 mL), EtOH (3 mL) and 1 M aqueous Na2CO3 solution (0.96 mL, 0.96 mmol) was added (PPh3)2PdCl2 (27 mg, 0.04 mmol) in one portion. The mixture was heated in the dark to 105° C. under a nitrogen atmosphere for 20 h, filtered through a pad of cotton wool and concentrated. The residue was purified by PTLC with CH2Cl2:MeOH=98:2 as eluent to afford styrene 28 (51 mg, 46%) as a pale yellow solid. 1H NMR (400 MHz; CDCl3) δ 6.55 (dd, J=2.0, 3.5 Hz, 1H), 7.15 (d, J=16.3 Hz, 1H), 7.31 (d, J=16.3 Hz, 1H), 7.35 (m, 1H), 7.62 (s, 4H), 8.13 (d, J=1.8 Hz, 1H), 8.50 (m, 1H), 9.17 (br s, NH).

Workup

filtrationfiltered through a pad of cotton wool
concentrationconcentrated
customThe residue was purified by PTLC with CH2Cl2

Sources & evidence

ORD record: ord-0c18c5b8591c41438a324ca3884c4741
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652137B2

Reaction notes

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