Sodium Carbonate → HCID 123984127, compound

HRID 1772733Notes

Reaction equation

HRID 1772733 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:37]2[CH:42]=[CH:41][C:40]([N:43]3[C:47](=[O:48])[N:46]([CH2:49][O:50][CH2:51][CH2:52][Si:53]([CH3:56])([CH3:55])[CH3:54])[CH:45]=[N:44]3)=[CH:39][CH:38]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>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].C(Cl)Cl>[O:26]1[CH2:27][CH2:28][N:23]([C:5]2[C:6]3[N:7]([CH:8]=[C:9]([CH2:11][CH2:12][C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[N:10]=3)[C:2]([C:37]3[CH:38]=[CH:39][C:40]([N:43]4[C:47](=[O:48])[N:46]([CH2:49][O:50][CH2:51][CH2:52][Si:53]([CH3:56])([CH3:55])[CH3:54])[CH:45]=[N:44]4)=[CH:41][CH:42]=3)=[CH:3][N:4]=2)[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1177278954-(5-Bromo-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-8-yl)morpholineHCID 124003847HCID 124003847, compound

Product 1

HCID 123984127HCID 123984127, compound

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

A mixture of compound 3a (102 mg, 0.233 mmol), compound 84d (97.1 mg, 0.233 mmol, PdCl2(dppf)-DCM (5.7 mg, 0.0070 mmol), and Ar-degassed aqueous 2M Na2CO3 (0.582 mL, 1.16 mmol) in Argon-degassed 1,4-dioxane (4 mL) was further degassed with Argon for 3 min and then stirred at 90° C. for 5 h. After cooling to rt, the reaction mixture was concentrated under reduced pressure to a brown oil which was purified by flash column chromatography on silica gel (40-100% EtOAc-DCM, followed by 100% EtOAc) to afford compound 84e as a crystalline white solid. Mass spectrum (LCMS, ESI pos.): Calcd. for C35H40N8O3Si, 649.3 (M+H). found 649.6.

Workup

  1. customdegassed 1,4-dioxane (4 mL)
  2. customwas further degassed with Argon for 3 min
  3. temperatureAfter cooling to rt
  4. concentrationthe reaction mixture was concentrated under reduced pressure to a brown oil which
  5. customwas purified by flash column chromatography on silica gel (40-100% EtOAc-DCM, followed by 100% EtOAc)

Sources & evidence

ORD record
ord-10ebf667c43b4e63abb5f28df53768cc
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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