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

Potassium Carbonate → 4,6-difluoro-5-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1H-indole-3-carbaldehyde

HRID 1054635
Notes
Print preview

Reaction equation

HRID 1054635 reaction equation
CC1(C)COB([C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])=[CH:10][CH:9]=2)OC1.Br[C:21]1[C:22]([F:33])=[C:23]2[C:27](=[CH:28][C:29]=1[F:30])[NH:26][CH:25]=[C:24]2[CH:31]=[O:32].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CCO.O.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]>[F:33][C:22]1[C:21]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([CH3:17])([CH3:18])[CH2:15][OH:16])=[CH:12][CH:13]=2)=[C:29]([F:30])[CH:28]=[C:27]2[C:23]=1[C:24]([CH:31]=[O:32])=[CH:25][NH:26]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 866985785-Bromo-4,6-difluoro-1H-indole-3-carbaldehydeHCID 866986392-(4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)-2-methylpropan-1-ol

Product 1

HCID 866986404,6-difluoro-5-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1H-indole-3-carbaldehydeYield 32%

Reagents, catalysts & solvents 4

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 702EthanolSolvent
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Procedure

To a solution of 2-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]-2-methylpropan-1-ol (102 mg, 0.386 mmol) and 5-bromo-4,6-difluoro-1H-indole-3-carbaldehyde (100 mg, 0.386 mmol) in toluene (6 mL) and EtOH (2 mL) was added a solution of potassium carbonate (160 mg, 1.159 mmol) in water (1.0 mL) and Pd(dppf)Cl2 (15.8 mg, 0.019 mmol) at room temperature under N2. The reaction was cooled to room temperature, and extracted with ethyl acetate (10 mL×2). The organic layers were washed with brine (10 mL), and dried over sodium sulfate and concentrated to give a crude residue, which was purified by column chromatography to give the title compound (40 mg, 32%) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 10.0 (s, 1 H), 8.13 (s, 1 H), 7.51 (d, 2 H), 7.40 (d, 2 H), 7.19 (d, 1 H), 3.63 (s, 2 H), 1.36 (s, 6 H).

Workup

  1. extractionextracted with ethyl acetate (10 mL×2)
  2. washThe organic layers were washed with brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a crude residue, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-75cd2b174edc49e4baa40e7cd6f64bef
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394285B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes