Sodium Carbonate → HCID 59699975, compound

HRID 2234551Notes

Reaction equation

HRID 2234551 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[OH:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>Cl[Pd-2](Cl)(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.ClCCl.C(#N)C>[CH:11]1([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:21]4[CH:22]=[C:17]([OH:16])[CH:18]=[CH:19][CH:20]=4)[CH:3]=3)[NH:8][CH:9]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 59699856HCID 59699856, compound

Product 1

HCID 59699975HCID 59699975, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 178418903HCID 178418903, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromo-3-cyclopentyl-1H-pyrrolo[2,3-b]pyridine (31.8 mg, 0.12 mmol), 3-hydroxyphenylboronic acid (33.1 mg, 0.24 mmol) and 4.2 mg (5 mol %) of dichlorobis(triphenylphosphino)palladium(II) were placed in a vial and 0.8 ml of acetonitrile and 0.8 ml of a 2M aqueous solution of sodium carbonate were added and the mixture irradiated in a Personal Chemistry® microwave reactor to 150° C. for 900 seconds. The resulting mixture was distributed between 15 mL of a saturated aqueous solution of sodium bicarbonate and 30 mL of dichloromethane. The organic phase was dried over sodium sulfate and evaporated. The crude was purified via silica gel chromatography using a gradient of ethyl acetate in hexanes to give 3-(3-Cyclopentyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenol (4.5 mg, 14% yield) as off white powder. 1H NMR (500 MHz, CD3OD) δ 8.36 (s, 1H), 8.14 (d, 2 Hz, 1H), 7.29 (t, 8 Hz, 1H), 7.19 (s, 1H), 7.10 (d, 7 Hz, 1H), 7.06 (s, 1H), 6.79 (dd, 2 Hz, 8 Hz, 1H), 2.1 (m, 2H), 1.94 (m, 2H), 1.8 (m, 4H), 1.37 (m, 1H). MS: m/z 279.1 [MH+].

Workup

  1. additionwere added
  2. customthe mixture irradiated in a Personal Chemistry® microwave reactor to 150° C. for 900 seconds
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated
  5. customThe crude was purified via silica gel chromatography

Sources & evidence

ORD record
ord-fac0baf48c6c49d3b5edded33a6f45f0
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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