HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 2281057
Notes
Print preview

Reaction equation

HRID 2281057 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 114020504-(Hydroxymethyl)benzeneboronic acid pinacol esterHCID 709780934-Bromo-5-iodo-1-(2-methylpropyl)-1H-benzotriazole

Product 1

HCID 68657365{4-[4-bromo-1-(2-methylpropyl)-1H-benzotriazol-5-yl]phenyl}methanol

Reagents, catalysts & solvents 4

HCID 178418807
HCID 178418807, compound
Catalyst
HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

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

  1. customThe vessel was sealed
  2. temperatureThe mixture was cooled to ambient temperature
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo
  5. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes