Potassium Fluoride → HCID 71284878, compound

HRID 1481786Notes

Reaction equation

[CH2:1]([O:8][C:9]1[N:24]=[C:23](Br)[C:22]([OH:26])=[C:21]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][N:36]1[C:44]2[C:39](=[CH:40][C:41](B(O)O)=[CH:42][CH:43]=2)[CH:38]=[CH:37]1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[K+]>C1COCC1.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]>[CH2:1]([O:8][C:9]1[N:24]=[C:23]([C:41]2[CH:40]=[C:39]3[C:44](=[CH:43][CH:42]=2)[N:36]([CH3:35])[CH:37]=[CH:38]3)[C:22]([OH:26])=[C:21]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of benzyl 2,4-bis(benzyloxy)-6-bromo-5-hydroxynicotinate (0.23 g, 0.44 mol), 1-methyl-1H-indol-5-ylboronic acid (90 mg, 0.51 mmol), Pd2(dba)3 (20 mg, 0.022 mmol), tri-tert-butylphosphonium tetrafluoroborate (13 mg, 0.044 mmol) and KF (0.26 g, 4.4 mmol) in THF (2.0 mL) was stirred at 60° C. overnight under an Ar atmosphere. The mixture was filtered. The filtrate was evaporated and purified by silica chromatography (2-30% ethyl acetate in hexanes) to give benzyl 2,4-bis(benzyloxy)-5-hydroxy-6-(1-methyl-1H-indol-5-yl)nicotinate (0.24 g, 96%).

Workup

filtrationThe mixture was filtered
customThe filtrate was evaporated
custompurified by silica chromatography (2-30% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-a7cf1e6d735d4a3a8377175a7973dad5
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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