Sodium Carbonate → 5-(2-Phenoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 1432325Notes

Reaction equation

C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[C:12]([C:20]#[N:21])=[CH:11]2)(=O)=O)C=CC=CC=1.[O:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CCO.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>[O:22]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=1[C:17]1[CH:18]=[C:13]2[C:12]([C:20]#[N:21])=[CH:11][NH:10][C:14]2=[N:15][CH:16]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of 8 (40.0 mg, 0.11 mmol), 2-phenoxyphenylboronic acid (35.5 mg, 0.166 mmol), PdCl2(PPh3)2 (7.8 mg, 0.011 mmol), LiCl (14.0 mg, 0.33 mmol), 1M Na2CO3 (276 μL, 0.28 mmol) in EtOH (0.66 mL) and toluene (0.66 mL) was heated at 105° C. for 0.5 h in a sealed reaction tube. Reaction mixture was separated between ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate (2×). The combined organic solutions were concentrated and purified by PTLC using ethyl acetate:hexane (1:1) as eluent to give 9 as a white solid (13.8 mg, 40%); 1H NMR (400 MHz, CDCl3) δ 12.80-12.60 (bs, NH), 8.69 (d, J=2.0 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 7.87 (s, 1H), 7.53 (dd, J=7.6, 1.7 Hz, 1H), 7.40 (dt, J=7.5, 1.8 Hz, 1H), 7.29 (m, 3H), 7.06 (m, 2H), 6.94 (m, 2H); MS (CI) m/z 352.8 (MH+MeCN).

Workup

customReaction mixture
customwas separated between ethyl acetate and brine
extractionThe aqueous layer was extracted with ethyl acetate (2×)
concentrationThe combined organic solutions were concentrated
custompurified by PTLC

Sources & evidence

ORD record: ord-20bc22df7e4b4a9b81ad04896247c8d1
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612086B2

Reaction notes

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