Sodium Carbonate → HCID 86724307, compound

HRID 594903Notes

Reaction equation

HRID 594903 reaction equation
C(OC([N:8]([C:16]1[O:17][CH2:18][C:19]2([C:29]3[C:24](=[CH:25][CH:26]=[C:27](B4OC(C)(C)C(C)(C)O4)[CH:28]=3)[O:23][CH2:22][C:21]32[CH2:40][CH2:39]3)[N:20]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.Br[C:42]1[CH:43]=[C:44]2[CH:50]=[CH:49][NH:48][C:45]2=[N:46][CH:47]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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>[NH:48]1[C:45]2=[N:46][CH:47]=[C:42]([C:27]3[CH:28]=[C:29]4[C:19]5([CH2:18][O:17][C:16]([NH2:8])=[N:20]5)[C:21]5([CH2:39][CH2:40]5)[CH2:22][O:23][C:24]4=[CH:25][CH:26]=3)[CH:43]=[C:44]2[CH:50]=[CH:49]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 86724308HCID 86724308, compound

Product 1

HCID 86724307HCID 86724307, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

The mixture of di-tert-butyl[6′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]oxazol]-2″-yl]imidodicarbonate (140 mg, 0.25 mmol), 5-bromo-1H-pyrrolo[2,3-b]pyridine (87 mg, 0.44 mmol), Pd(PPh3)4 (58 mg, 0.050 mmol), and Na2CO3 (80 mg, 0.76 mmol) in 1,4-dioxane-H2O (2.8 ml, 4:1) was stirred for 7 hours at 100° C. After dilution with EtOAc and H2O, the organic layer was washed with H2O, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (CHCl3:MeOH=100:0-85:15) to give white solid. The solid was washed by diisopropyl ether to give 6′-(1H-pyrrolo[2,3-b]pyridin-5-yl)dispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]oxazol]-2″-amine (42 mg).

Workup

  1. washAfter dilution with EtOAc and H2O, the organic layer was washed with H2O
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (CHCl3:MeOH=100:0-85:15)
  5. customto give white solid
  6. washThe solid was washed by diisopropyl ether

Sources & evidence

ORD record
ord-09a1d134baa5454fb7aa05a7a82d311b
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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