Cesium carbonate → {4-[4-bromo-1-(2-methylpropyl)-1H-benzotriazol-5-yl]phenyl}methanol

HRID 2281057Notes

Reaction equation

[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1I.[OH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:21]1[CH:22]=[CH:23][C:18]([CH2:17][OH:16])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 40 °C

Procedure

4-Bromo-5-iodo-1-(2-methylpropyl)-1H-benzotriazole (554 mg, 1.458 mmol), 4-(hydroxymethyl)benzeneboronic acid pinacol ester (325 mg, 1.388 mmol), PdCl2(dppf)-dichloromethane adduct (56.7 mg, 0.069 mmol) and cesium carbonate (1357 mg, 4.16 mmol) were combined in tetrahydrofuran (7 ml) and water (0.700 ml). The vessel was sealed and heated at 40° C. for 48 hours. The mixture was cooled to ambient temperature, diluted with ethyl acetate, filtered through Celite and concentrated in vacuo. The residue was purified via silica gel chromatography (ethyl acetate/hexane gradient), providing the titled compound as white foam. LRMS m/z (M+H) 359.9 and 361.9 found, 360.06 and 362.06 required.

Workup

customThe vessel was sealed
temperatureThe mixture was cooled to ambient temperature
filtrationfiltered through Celite
concentrationconcentrated in vacuo
customThe residue was purified via silica gel chromatography (ethyl acetate/hexane gradient)

Sources & evidence

ORD record: ord-d562e9bea4b4490e9317de3b39706036
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139576B2

Reaction notes

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