Sodium Carbonate → HCID 9844427, compound

HRID 650971Notes

Reaction equation

Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][C@H:13]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])[O:12][C:11]2=[O:20])=[CH:6][C:5]=1[F:21].[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)=[O:26].C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.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]>[C:17]([NH:16][CH2:15][C@@H:13]1[O:12][C:11](=[O:20])[N:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]#[C:2][C:30]3[CH:31]=[CH:32][C:27]([C:25]([O:24][CH3:23])=[O:26])=[CH:28][CH:29]=3)=[C:5]([F:21])[CH:6]=2)[CH2:14]1)(=[O:19])[CH3:18]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of Example 1E (55 mg), 4-methoxycarbonylphenylboronic acid (27.2 mg), and tris(dibenzylideneacetone)dipalladium (15 mg) in degassed dimethoxyethane (1.3 mL) was treated with 2N aqueous Na2CO3 (0.1 mL), heated to 70° C. for 20 hours, and concentrated. The concentrate was dissolved in dichloromethane (2 mL), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 1:1 hexanes/acetone to provide the desired product. MS (ESI(+)) m/e 411 (M+H)+; MS (ESI(−)) m/e 409 (M−H)−; 1H NMR (300 MHz, CDCl3) δ 8.00 (d, 2H), 7.61 (d, 2H), 7.55 (dd, 1H), 7.50 (t, 1H), 7.20 (dd, 1H), 6.0 (br t, 1H), 4.80 (m, 1H), 4.07 (t, 1H), 3.93 (s, 3H), 3.85-3.75 (dd, 1H), 3.60-3.50 (m, 2H), 2.05 (s, 3H).

Workup

concentrationconcentrated
dissolutionThe concentrate was dissolved in dichloromethane (2 mL)
filtrationfiltered
concentrationconcentrated
customThe concentrate was purified by flash column chromatography on silica gel with 1:1 hexanes/acetone

Sources & evidence

ORD record: ord-86b5dbff8744451bb148604415b894b7
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06277868B1

Reaction notes

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