Sodium Carbonate → HCID 86715470, compound

HRID 2284562Notes

Reaction equation

HRID 2284562 reaction equation
Br[C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[O:15]1[CH2:20][CH2:19][O:18][CH2:17]C1>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:15]1[C:20]2[CH:3]=[C:2]([C:2]3[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=3)[CH:7]=[CH:6][C:19]=2[O:18][CH2:17]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 6933243-Bromo-2-chloropyridine

Product 1

HCID 86715470HCID 86715470, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Analogous to the preparation of 5-(2-chloropyridin-3-yl)-1H-indazole,3-(benzo[d][1,3]dioxol-6-yl)-2-chloropyridine was prepared by heating the mixture of 3,4-(methylenedioxy)phenyl boronic acid (3.0 g, 18.1 mmol), 3-bromo-2-chloropyridine (4.2 g, 1.8 mmol), Pd(PPh3)4 (1.2 g, 1.0 mmol) and 2M aq. Na2CO3 (27 mL, 54 mmol) in 1,4-dioxane (125 mL) under argon atmosphere for 12 h. LC/MS indicated three products. The crude concentrate that was obtained after the extractive work-up dissolved in CH2Cl2, adsorbed on to silica gel and dried. Subsequent purification by flash silica gel column chromatography (Combiflash® companion System® with RediSep® silica gel column 120 g, 30-70% EtOAC/hexanes eluting solvent gradient upon dry powder loading) provided 3-(benzo[d][1,3]dioxol-6-yl)-2-chloropyridine as a white solid 2.3 g, (38%). 1H NMR (DMSO-d6): δ 8.38 (dd, 1H, J=1.7 and 4.7 Hz), 7.82 (dd, 1H, J=2.0 and 7.6 Hz), 7.47 (dd, 1H, J=4.7 and 7.6 Hz), 7.05 (d, 1H, J=1.7 Hz), 7.01 (d, 1H, J=7.9 Hz), 6.90 (dd, 1H, J=1.7 and 7.9 Hz), 6.07 (s, 2H LCMS: rt 7.27 min (A), purity 96%, MS (m/e) 234 (MH+).

Workup

  1. customwas prepared
  2. temperatureby heating
  3. concentrationThe crude concentrate that
  4. customwas obtained after the extractive work-up
  5. customdried
  6. customSubsequent purification
  7. dry with materialby flash silica gel column chromatography (Combiflash® companion System® with RediSep® silica gel column 120 g, 30-70% EtOAC/hexanes eluting solvent gradient upon dry powder loading)

Sources & evidence

ORD record
ord-491af596764d48d99a674ac845ab1e44
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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